Pyridine → HCID 86664961, compound

HRID 576446Notes

Reaction equation

HRID 576446 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:8][CH2:9][OH:10])=[CH:5][S:6][CH:7]=1.N1C=CC=CC=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH2:8][CH2:9][O:10][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])=[CH:5][S:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 46832003HCID 46832003, compound

Product 1

HCID 86664961HCID 86664961, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 500 ml three-necked flask (reaction container) with thermometer and dropping funnel, 7.72 g (48.8 mmol) of 2-(4-methoxythiophene-3-yl)ethane-1-ol represented by the formula (VI-A) shown below, 11.58 g (146 mmol) of pyridine, and 135 ml of methylene chloride were transferred. The reaction container (flask) was cooled in an ice bath, then 50 ml of methylene chloride containing 18.6 g (97.6 mmol) of p-toluene sulfonic chloride was added dropwise over a period of 10 minutes, then the ice bath was removed from the flask. The reaction solution was stirred at room temperature for a period of 1.5 hours. After the reaction was completed, 100 ml of water was added to separate the organic layer from the water layer. The organic layer was washed twice each with 100 ml of water, then washed twice with saturated aqueous sodium hydrogen carbonate and then dried over anhydrous sodium sulfate. Then it was condensed under a reduced pressure, thereby obtaining a crude product. This crude product was purified using silica gel column chromatography to obtain p-toluene sulfonic acid-2-(4-methoxythiophene-3-yl)ethyl ester (10.5 g, 33.6 mmol, yield 68.9%), a thiophene derivative represented by the formula (IV-A) having properties described below. The chemical equation (X-A) is shown below.

Workup

  1. customInto a 500 ml three-necked flask (reaction container) with thermometer
  2. temperatureThe reaction container (flask) was cooled in an ice bath
  3. customthe ice bath was removed from the flask
  4. addition100 ml of water was added
  5. customto separate the organic layer from the water layer
  6. washThe organic layer was washed twice each with 100 ml of water
  7. washwashed twice with saturated aqueous sodium hydrogen carbonate
  8. dry with materialdried over anhydrous sodium sulfate
  9. customcondensed under a reduced pressure
  10. customobtaining a crude product
  11. customThis crude product was purified

Sources & evidence

ORD record
ord-1caa35f6aa2d4a218daf37fc7d9fce40
Source dataset
uspto-grants-2015_05
Patent number
US09039936B2

Reaction notes

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